153033-31-9Relevant articles and documents
Sterically encumbered bipyridyl-derivatized conjugated polymers and metallopolymers incorporating phenylenevinylene, phenyleneethynylene, and fluorenylene segments
He, Susan,Buelt, Ashley A.,Hanley, Jessica M.,Morgan, Brad P.,Tennyson, Andrew G.,Smith, Rhett C.
, p. 6344 - 6352 (2012)
This work reports the preparation of a series of 2,2′-bipyridyl (bipy) modified π-conjugated polymers having an average of one or three monomer units (p-arylene ethynylene for PPE1 and PPE3 or 7,7-dihexylfluorene for PF1 and PF3) between metal-binding sites. Spectroscopic data demonstrate that strategic placement of sterically encumbered mesityl groups about the metal binding sites enforces a 1:1 metal to bipy binding ratio. This steric coordination control ensures that the metalated polymers remain solution processable rather than forming insoluble networks via coordinative cross-linking. The solution photophysical and electrochemical properties of metal-free and metalated materials are reported and compared with those of related conjugated polymers and conducting metallopolymers.
Ferrocene metallopolymers of intrinsic microporosity (MPIMs)
Ambrose, Kenson,Feldblyum, Jeremy I.,Nyayachavadi, Audithya,Rondeau-Gagné, Simon,Walter, Kelly G.,Zhai, Tianran
supporting information, p. 238 - 241 (2022/01/06)
We show here that non-network metallopolymers can possess intrinsic microporosity stemming from contortion introduced by metallocene building blocks. Metallopolymers constructed from ferrocenyl building blocks linked by phenyldiacetylene bridges are synth
Linker-Dependent Singlet Fission in Tetracene Dimers
Korovina, Nadezhda V.,Joy, Jimmy,Feng, Xintian,Feltenberger, Cassidy,Krylov, Anna I.,Bradforth, Stephen E.,Thompson, Mark E.
supporting information, p. 10179 - 10190 (2018/07/30)
Separation of triplet excitons produced by singlet fission is crucial for efficient application of singlet fission materials. While earlier works explored the first step of singlet fission, the formation of the correlated triplet pair state, the focus of
Tuning the moisture and thermal stability of metal-organic frameworks through incorporation of pendant hydrophobic groups
Makal, Trevor A.,Wang, Xuan,Zhou, Hong-Cai
, p. 4760 - 4768 (2013/12/04)
An isostructural series of NbO-type porous metal-organic frameworks (MOFs) with different dialkoxy-substituents of formula Cu2(TPTC-OR) (TPTC-OR = 2′,5′-di{alkyl}oxy-[1,1′:4′,1″-terphenyl]-3, 3″,5,5″-tetracarboxylate, R = Me, Et, nPr, nHex) has been synthesized and characterized. The moisture stability of the materials has been evaluated, and a new superhydrophobic porous MOF has been identified. The relationship between pendant side chain length and thermal stability has been analyzed by in situ synchrotron powder X-ray diffraction, showing decreased thermal stability as the side chain length is increased, contradictory to thermogravimetric decomposition studies. Additionally, the four materials exhibit moderate Brunauer-Emmett-Teller (BET) and Langmuir surface areas (1127-1396 m2 g-1 and 1414-1658 m2 g -1) and H2 capacity up to 1.9 wt % at 77 K and 1 bar.
Alkyloxy substituted organic dyes for high voltage dye-sensitized solar cell: Effect of alkyloxy chain length on open-circuit voltage
Ko, Soo-Byung,Cho, An-Na,Kim, Mi-Jeong,Lee, Chang-Ryul,Park, Nam-Gyu
experimental part, p. 88 - 98 (2012/04/04)
Three novel organic dyes (SB1, SB2, and SB3) containing 4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline as electron donor and cyanoacrylic acid as electron acceptor bridged by alkyloxy (methyl = SB1, propyl = SB2 and hexyl = SB3) substituted p-phenylenevinylene linkers have been synthesized. Density functional theory (DFT) has employed to study electron distribution and intramolecular charge transfer. Increase in alkyl chain length in alkyloxy substituent leads to increase in open-circuit voltage (V OC), which is found to be related to the increased electron lifetime at open-circuit condition. Under AM 1.5 G 1 sun light illumination (100 mW/cm2), an optimized SB3-sensitized cell show a short-circuit photocurrent density (JSC) of 12.83 mA/cm2, an open-circuit voltage (VOC) of 0.745 V and a fill factor (FF) of 0.64, corresponding to an overall conversion efficiency (η) of 6.12%. Little degradation in η observed over 40 days is indicative of long-term stability of the SB-series dyes.
A facile approach to highly efficient and thermally stable solid-state emitters: Knitting up AIE-active TPE luminogens by aryl linkers
Chan, Carrie Yin Kwan,Lam, Jacky Wing Yip,Zhao, Zujin,Deng, Chunmei,Chen, Shuming,Lu, Ping,Sung, Herman H.Y.,Kwok, Hoi Sing,Ma, Yuguang,Williams, Ian D.,Tang, Ben Zhong
, p. 949 - 958 (2013/01/15)
A facile approach to thermally stable and efficient solid-state emitters is proposed. By hooking up tetraphenylethene (TPE) units through aryl linkers under Suzuki coupling conditions, a series of arylene bis(tetraphenylethene)s (TPE-Ar-TPE Ar = 2, 5-dime
A facile approach to highly efficient and thermally stable solid-state emitters: Knitting up aie-active tpe luminogens by aryl linkers
Chan, Carrie Yin Kwan,Lam, Jacky Wing Yip,Zhao, Zujin,Deng, Chunmei,Chen, Shuming,Lu, Ping,Sung, Herman H. Y.,Kwok, Hoi Sing,Ma, Yuguang,Williams, Ian D.,Tang, Ben Zhong
, p. 949 - 958 (2014/01/17)
A facile approach to thermally stable and efficient solid-state emitters is proposed. By hooking up tetraphenylethene (TPE) units through aryl linkers under Suzuki coupling conditions, a series of arylene bis(tetraphenylethene)s (TPE-Ar-TPE Ar=2,5- dimeth
Synthesis and optical properties of molecular rods comprising a central core-substituted naphthalenediimide chromophore for carbon nanotube junctions
Grunder, Sergio,Munoz Torres, David,Marquardt, Christoph,Balaszczyk, Alfred,Krupke, Ralph,Mayor, Marcel
supporting information; experimental part, p. 478 - 496 (2011/03/22)
The synthesis of a series of molecular rods 1-5, designed to bridge the gap of a carbon nanotube junction in order to emit light as a characteristic signal of integrated molecules, is reported. The molecular rods consist of a central naphthalenediimide (NDI) core, which itself is substituted with benzylamino and benzylsulfanyl groups, providing distinct absorption and emission properties. The NDI core is embedded in an oligo(phenylene ethynylene) (OPE) system providing the rod-like structure required to bridge gaps between nanoelectrodes. The number of repeating units of the OPE is varied to adjust the length of the target compounds between 2.3 and 6.6 nm. The OPE parts are terminally functionalized with polyaromatic hydrocarbon groups (naphthalene, phenanthrene, anthracene or pyrene), which possess affinity with the surface of the carbon nanotubes due to van der Waals interactions. Synthetic protocols based on Sonogashira-Hagihara couplings were developed to build up the OPE backbone. Bifunctional iodophenyl acetylene derivative 33 served as a key building block in a coupling-deprotecting-coupling sequence. The NDI building block was synthesized by an aromatic nucleophilic substitution reaction of 2,6-dichloro-1,4,5,8-tetracarboxylic acid naphthalenediimide derivative 9 and the corresponding amine and sulfide (i.e., 11, 12), respectively. The convergent synthesis allows modular assembly of the NDI and OPE parts in a final Sonogashira-Hagihara coupling reaction. The target structures were fully characterized by NMR spectroscopy and mass spectrometry. Further, the optical properties of compounds 3-5 in solution, and on a graphene surface were qualitatively investigated. A Dexter-type energy transfer from the OPE unit to the NDI unit was observed. The studies of target structures 3-5 revealed that diamino-functionalized compound 3 is ideally suited for the envisaged single molecule electroluminescence experiments. The synthesis of a series of over 6-nm long modular rods with a central decoupled naphthalenediimide (NDI) chromophore isreported. Their spectroscopic properties are adjusted by varying the substituents of the NDI core
Bipolar copoly(aryl ether) containing distyrylbenzene, triphenylamine, and 1,2,4-triazole moieties: Synthesis and optoelectronic properties
Wu, Chia-Shing,Lee, Shawn-Lin,Chen, Yun
experimental part, p. 3099 - 3108 (2012/05/05)
A novel copoly(aryl ether) (P1) consisting of alternate emitting segments (distyrylbenzene) and a bipolar moiety composed of directly linked electron-transporting aromatic 1,2,4-triazole and hole-transporting triphenylamine was synthesized. The copoly(aryl ether) is readily soluble in common organic solvents and exhibit good thermal stability with thermal decomposition temperature above 450 °C. The emission and the photoluminescence quantum yield of the copolymer are dominated by the emitting segments (distyrylbenzene) with longer emissive wavelength. Electron affinity of P1 is evidently enhanced after introducing the isolated bipolar unit, as confirmed by the lowered lowest unoccupied molecular orbital level (-2.77 eV) relative to P0 without bipolar unit (-2.34 eV). This results in improved emission efficiency of its polymer light-emitting diode (indium tin oxide/poly(3,4-ethylene dioxythiophene):poly(styrene sulfonate)/P1/LiF/Ca/Al) due to more balanced charges injection and transport. Blending P1 with poly(9,9-dihexylfluorene) (PF) further improves the efficiency of the device; the best performance was obtained for PF/P1 = 20/0.8 (w/w) with maximum luminance and maximum luminance efficiency being significantly enhanced to 3260 cd/m2 and 1.08 cd/A, respectively, from 380 cd/m2 and 0.009 cd/A of P1-based device. These results demonstrate that the bipolar moiety can be used to enhance charges injection and transport of electroluminescent polymers.
Iterative synthesis of heterotelechelic oligo(phenylene-vinylene)s by olefin cross-metathesis
Norris, Benjamin N.,Pan, Tianqi,Meyer, Tara Y.
supporting information; experimental part, p. 5514 - 5517 (2011/03/18)
A novel iterative synthesis of heterotelechelic oligo(phenylene-vinylene)s using olefin cross-metathesis is reported. The metathesis homologation proceeds in good yields and allows for further functionalization, including the facile formation of donor-acceptor complexes and repeating sequence copolymers.
